Andrew Raycroft was bron May 4, 1980 in Belleville, Ontario. The fifth round, 135th overall selection of the Boston Bruins in the 1998 NHL Entry Draft, Raycroft is a graduate of the OHL's Kingston Frontenacs (1999-00) and Sudbury Wolves (1997-1999).

The OHL's Most Valuable Player in 1999-00, Raycroft became the first goaltender in 50 years to earn that honour and was named the top goaltender in the CHL. Following a MVP season in 1999-00, Raycroft joined the Bruins AHL affiliate in Providence for the 2000-01 season. Even though he spent the majority of the year in Providence, the Belleville native suited up for 15 games with the Bruins that year and over the course of the next two seasons was a workhorse with the baby Bruins.